Executive Assistant to Chief of Staff – Growth Track

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About the role

  • Executive Operations assistant protecting an education and software CEO’s time through calendar, accountability, hiring, and project management. Performance-based path to Chief of Staff.

Responsibilities

  • Own and optimize the CEO’s calendar, protecting deep-work blocks and aligning schedules with company goals
  • Run internal follow-ups, action items, reminders, escalations, and communications across Slack, WhatsApp, and email
  • Build and manage the company operating system using Trello, Asana, Notion, or similar tools
  • Track project owners, deadlines, next actions, and definitions of done
  • Hold leaders and teams accountable for deliverables and reporting cadence
  • Run end-to-end hiring operations, including pipeline management, scheduling, scorecards, assignments, Loom reviews, and references
  • Oversee content operations for YouTube, Instagram, and email without creating content
  • Track weekly content output, deadlines, approvals, and delivery
  • Collect monthly P&L data, KPI dashboards, and weekly reports
  • Analyze profit and loss statements and payroll, and provide recommendations on raises, compensation structures, inefficiencies, and staffing
  • Execute personal and local projects supporting business performance, such as managing a home studio build-out
  • Advise department leaders on practical AI use in their daily responsibilities
  • Complete scheduling, meeting notes, and action-item tasks during onboarding
  • Progress from execution and systems ownership into Chief of Staff-style planning, cross-functional problem-solving, and high-priority initiative management

Requirements

  • Highly organized and extremely self-accountable
  • Strong project management skills; experience with Trello, Asana, or similar tools
  • Exceptional attention to detail
  • Strong writing and communication skills, including detailed reports and clear, direct updates
  • Ability to make good decisions independently and anticipate needs
  • Ability to hold people accountable and handle tough conversations
  • Discretion, trustworthiness, and comfort with high confidentiality and sensitive information
  • Comfort with high access and high expectations
  • Experience or fluency using AI tools in daily workflows; at minimum, ChatGPT instead of Google
  • Familiarity with Google Workspace, Slack, Trello/Asana, Calendly, Zoom, and Loom
  • Spanish preferred but not required
  • Strong overlap with EST working hours
  • Must complete a required 5-minute camera-on Loom video submission
  • Must complete the final assignment involving a Google document and embedded YouTube videos

Benefits

  • Performance bonus
  • High-speed CEO training and full context into CEO decision-making
  • Growth track to Chief of Staff over 12–18 months, performance-based
  • Remote work with strong overlap with EST working hours

Job type

Full Time

Experience level

Lead

Salary

$60,000 - $170,000 per year

Degree requirement

No Education Requirement

Location requirements

RemoteUnited States

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